CA1226213A - Antimicrobial compositions - Google Patents
Antimicrobial compositionsInfo
- Publication number
- CA1226213A CA1226213A CA000437379A CA437379A CA1226213A CA 1226213 A CA1226213 A CA 1226213A CA 000437379 A CA000437379 A CA 000437379A CA 437379 A CA437379 A CA 437379A CA 1226213 A CA1226213 A CA 1226213A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- amine oxide
- compositions
- chlorhexidine
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Abstract of the Disclosure Antimicrobial compositions comprising a bis-biguanide compound and an amine oxide.
Description
~ZZ6213 ANTIMICROBIAL COMPOSITIONS
BACKGROUND OF THE INVENTION
The present invention relates to compositions useful as antimicrobial agents. More particularly, it relates to the enhancement of the activity of specific bus biguanide antimicrobial compounds by the addition of amine oxides.
Numerous antimicrobial agents and compositions have been described in the literature and these compounds have attained widespread utility, for example, as preservatives in the cosmetic and pharmaceutical area as well as for cleansing purposes. Such compositions to be useful should demonstrate high activity against a wide range of organ nisms while exhibiting low toxicity as well as being free from odor, easily handled and chemically stable. Not with-standing the widespread acceptance of such compositions, there is an ongoing search for more effective anti micro-blat agents and compositions and, therefore, there is anteed to enhance the antimicrobial activity of known anti-microbial agents by the addition of other compounds.
One of the objects of the present invention is to provide a method of enhancing the antimicrobial effect of come pounds having known antimicrobial activity.
Another object of this invention is to provide an anytime-crabbily composition comprising one or more antimicrobial compounds in combination with a compound which enhances the antimicrobial activity of the antimicrobial compound.
A still further object of this invention is to provide antimicrobial compositions effective against both gram positive bacteria and gram negative bacteria.
Swiss These and other objects of the invention will become apparent from the following description.
SUMMARY OF THE INVENTION
In accordance with the present invention, there is pro-voided compositions useful as antimicrobial agents comprise in (A) a bis-biguanide compound selected from the group consisting of polyhexamethylene biguanide hydrochloride and chlorhexidine salts, and (B) an amine oxide.
The enhancing effect on the antimicrobial properties is most remarkable when component (A) is employed with component (El) within specific ratios and the compositions lo of the invention can be employed as antimicrobial agents in various personal care products.
DETAILED DESCRIPTION
There are employed as the bis-biguanide compound, a compound selected from the group consisting of po~ybexamethylene ~iguanide hydrochloride of the formula:
25 HC~-NHz~CH3)3~(CH2)3~NH~C~NH~C~NH~(CH2)3~n(CH~)3~NNH~C~NH~CN
NH NH-HCl NH
wherein n is from 4.5 to 6.5, and chlorhexidine salts of on 1,6-di-(4-chlorophenylbiguanide)-hexane of the formula:
Of NH-C-NH-C-NH-(CH2)6NH-C-NH-f-NH I
NH NH No The salts which are useful include chlorhexidine acetate, chlorhexidine huddler and chlorhexidine gluconate.
These compounds may be employed alone or in mixtures.
JBP 2 , ~ZZ6Z~3 The polyhexamethylene biguanide hydrochloride are avail-able commercially, for example, from ICY Americas Inc.
Wilmington, Delaware under the a~e~n~me-kCosmocil CQ and the chlorhexidine salts are also available commercially, for example, from ICY Americas Inc., Wilmington, Delaware under the trade name, Chlorhexidine. The bis-biguanides should be present in the compositions of the present invention from about 2 to 5% by weight of the total composition, preferably from about 3 to I
The amine oxides which are useful in the compositions of the present invention are the amidoamine oxides of the formula:
O H SHEA
if l l R-C-N-(CH2)3-N - JO
SHEA
wherein R is from 7 to 17 carbon atoms or mixtures thereof.
The amidoamine oxides are available commercially, for example, from Lyons Chemical Company, Fair lawn, New Jersey under the trade name Barlow C and from Onyx Chemical Company, Jersey City, New Jersey under the trade name Ammonyx COO. The amidoamine oxides should be present in the compositions of the present invention from about 1 to 20% by weight of the total composition, preferably from about 4 to 8%.
In order to obtain the desired results of the present invention the amidoamine oxide to bis-biguanide ratio should be from about 1:2 to 4:1. If the ratio is less than about 1:2 the enhancement effect of the amidoamine oxide begins to diminish and if the ratio is greater than about 4:1, the resulting compositions tend to become harsh to the user and also are relatively expensive.
JBP 22-i 12Z6Z~L3 The balance of the compositions consist of water and may also contain minor amounts of owner components normally found in such compositions such as chelating agents, thickening agents, fragrances, coloring agents and the like.
The pi of the compositions should be maintained with-in a range of from about 4 to 8, preferably 7.0 to 7.5.
The present invention is more particularly described and explained by means of the following examples:
EXAMPLE I
An antimicrobial composition is prepared as follows:
a Methuselah (hydroxypropyl methyl cellulose) solution containing 1.9 g., active sufficient to provide 0.75%
wow Methuselah in the finished product is added to 75 g. deionized water and mixed until homogeneous. To this solution is added 50 g. active of a 20% active polyhexamethylene biguanide hydrochloride sold under the trade name Cosmocil CQ by ICY Americas Inc., Wit-mington, Delaware, followed by the addition of 0.25g. Versene 100 and 16.75 g. of 30% active cocoamido-propyldimethyl amine oxide. The pi is adjusted to 6.0 using 15% Hal and the total is adjusted to 250 g.
by the addition of deionized water. The resulting composition is of the following formula:
% w/w Cosmocil CQ 4.00 Versene 100 0.03 hydroxypropyl methyl cellulose 0.75 cocoamidopropyldimethyl 2.00 amine oxide deionized water us to 100 --- r ~226Z~3 EXAMPLE II
An antimicrobial composition is prepared according to the procedure of Example I except the cocoamidopropyldimethyl amine oxide is eliminated and replaced with deionized water.
EXAMPLE III
An antimicrobial composition is prepared according to the procedure of Example I except the Cosmocil CQ is elm-noted and replaced with deionized water EXAMPLE IV
An antimicrobial composition is prepared according to thepr~cedure of Example I except that 33.25 g. of cocoamido-propyldimethyl amine oxide are utilized resulting in a 1:1 ratio of amine oxide to Cosmocil CQ (on an "active"
basis).
EXAMPLE V
An antimicrobial composition is prepared according to the procedure of Example I except that 66.6 g. of amine oxide are utilized resulting in a 2:1 ratio of amine oxide to Cosmocil CQ (on an "active" basis).
EXAMPLE VI
A screening technique is used to test the compositions in Examples I-V. This technique consists of preparing 2-fold or 4-fold serial dilutions of the compositions of each Example. Allocates of these dilutions are then inoculated with a mixed suspension of gram positive bacteria or a mixed suspension of gram negative bacteria. The inoculm JBP I
1~26Z~3 density is adjusted to yield approximately 107 bacteria/ml of sample. Portions of the inoculated sample are then tested for viable bacteria at zero-time (immediately after inoculation), 6 to 8 minutes, 15 minutes, 30 minutes and 60 minutes after inoculation. This testing involves placing a calibrated 0.01 ml transfer loop into the inoculated sample and removing a remeasured portion which is then streaked on a solid growth medium (ajar) and incubated for a period of 48 hours at a temperature of 35~C. After the incubated period, the plates are examined for the presence or absence of growth. Any amount of growth on the line of streak is considered as positive growth. When the compositions of Examples I-V are tested according to the above procedure the following results are lo obtained. These results are expressed in terms of the minimum inhibitory concentration required for complete kill expressed in micrograms per milliliter (mcg/ml).
TABLE I
Composition Gram Positive Gram Negative time minutes time minutes Example I >104 104 156 39 <19 2500 312 39 <19 <19 Example II >104 5000 625 78 156 2500 39 <19 <19 <19 Example III >104 >104 5000 1250 1250 >104 >104 >104 >104 >104 Example IV >104 625 19 <19 <19625 <19 <19 ~19 <19 Example V >10 4 1250 19 <19 it 5000 <19 <19 <19 <19 ~ZZ~Z~3 These results clearly demonstrate the antimicrobial ad van-taxes of the compositions of the present invention, i.e., the compositions of Examples I, IV and V.
EXAMPLE VII
An antimicrobial composition is prepared according to the procedure of Example I and is of the following formulation:
wt/wt Chlorhexidine gluconate 4.00 Versene 100 0.03 15 hydroxypropylmethyl cellulose 0.75 cocoamidopropyldimethyl 4.00 deionized water us to 100 The pi of the above formulation is adjusted to l6.0 with dilute Hal.
EXAMPLE VIII
An antimicrobial composition is prepared according to the procedure of Example VII except that the cocoamidopropyl-dim ethyl amine oxide is utilized in a 1:2 ratio of amine oxide to chlorhexidine gluconate (on an "actves" basis).
EXAMPLE IX
An antimicrobial composition is prepared according to the procedure of Example VII except the cocoamidopropyldi-methyl amine oxide is eliminated and replaced with deionized water.
12;~6Z:~3 EXAMPLE X
An antimicrobial composition is prepared according to the procedure of Example VII except the chlorhexidine gluconate is eliminated and replaced with deionized water.
EXAMPLE XI
The compositions of Examples VII, VIII, IX and X are tested according to the procedure of Example VI and give the following results.
BP 2_.' - ~Z26Z~3 o o ox ox o o _ o o SHEA o Us r7 o us Al U') cry o Z O
En a N
I O
" I_ O
to Lo A
O Us O O O
O O O
ED Irk In Us I N
o a o H I O
O I O O
Eye I o o I_ Us Al a Jo I o o O O
En E QJ co a m o o 5 6 I o o I
PA
o o o o o o o o o A
C: H H
I) H X
I
Us O Q
I
O X X X X
.
lZ2~Z~3 Various other features and embodiments of the present invention not specifically set forth will be obvious to those skilled in the art, all of which may be achieved without departing from the spirit and scope of the invention as defined by the following claims.
JBP 22i
BACKGROUND OF THE INVENTION
The present invention relates to compositions useful as antimicrobial agents. More particularly, it relates to the enhancement of the activity of specific bus biguanide antimicrobial compounds by the addition of amine oxides.
Numerous antimicrobial agents and compositions have been described in the literature and these compounds have attained widespread utility, for example, as preservatives in the cosmetic and pharmaceutical area as well as for cleansing purposes. Such compositions to be useful should demonstrate high activity against a wide range of organ nisms while exhibiting low toxicity as well as being free from odor, easily handled and chemically stable. Not with-standing the widespread acceptance of such compositions, there is an ongoing search for more effective anti micro-blat agents and compositions and, therefore, there is anteed to enhance the antimicrobial activity of known anti-microbial agents by the addition of other compounds.
One of the objects of the present invention is to provide a method of enhancing the antimicrobial effect of come pounds having known antimicrobial activity.
Another object of this invention is to provide an anytime-crabbily composition comprising one or more antimicrobial compounds in combination with a compound which enhances the antimicrobial activity of the antimicrobial compound.
A still further object of this invention is to provide antimicrobial compositions effective against both gram positive bacteria and gram negative bacteria.
Swiss These and other objects of the invention will become apparent from the following description.
SUMMARY OF THE INVENTION
In accordance with the present invention, there is pro-voided compositions useful as antimicrobial agents comprise in (A) a bis-biguanide compound selected from the group consisting of polyhexamethylene biguanide hydrochloride and chlorhexidine salts, and (B) an amine oxide.
The enhancing effect on the antimicrobial properties is most remarkable when component (A) is employed with component (El) within specific ratios and the compositions lo of the invention can be employed as antimicrobial agents in various personal care products.
DETAILED DESCRIPTION
There are employed as the bis-biguanide compound, a compound selected from the group consisting of po~ybexamethylene ~iguanide hydrochloride of the formula:
25 HC~-NHz~CH3)3~(CH2)3~NH~C~NH~C~NH~(CH2)3~n(CH~)3~NNH~C~NH~CN
NH NH-HCl NH
wherein n is from 4.5 to 6.5, and chlorhexidine salts of on 1,6-di-(4-chlorophenylbiguanide)-hexane of the formula:
Of NH-C-NH-C-NH-(CH2)6NH-C-NH-f-NH I
NH NH No The salts which are useful include chlorhexidine acetate, chlorhexidine huddler and chlorhexidine gluconate.
These compounds may be employed alone or in mixtures.
JBP 2 , ~ZZ6Z~3 The polyhexamethylene biguanide hydrochloride are avail-able commercially, for example, from ICY Americas Inc.
Wilmington, Delaware under the a~e~n~me-kCosmocil CQ and the chlorhexidine salts are also available commercially, for example, from ICY Americas Inc., Wilmington, Delaware under the trade name, Chlorhexidine. The bis-biguanides should be present in the compositions of the present invention from about 2 to 5% by weight of the total composition, preferably from about 3 to I
The amine oxides which are useful in the compositions of the present invention are the amidoamine oxides of the formula:
O H SHEA
if l l R-C-N-(CH2)3-N - JO
SHEA
wherein R is from 7 to 17 carbon atoms or mixtures thereof.
The amidoamine oxides are available commercially, for example, from Lyons Chemical Company, Fair lawn, New Jersey under the trade name Barlow C and from Onyx Chemical Company, Jersey City, New Jersey under the trade name Ammonyx COO. The amidoamine oxides should be present in the compositions of the present invention from about 1 to 20% by weight of the total composition, preferably from about 4 to 8%.
In order to obtain the desired results of the present invention the amidoamine oxide to bis-biguanide ratio should be from about 1:2 to 4:1. If the ratio is less than about 1:2 the enhancement effect of the amidoamine oxide begins to diminish and if the ratio is greater than about 4:1, the resulting compositions tend to become harsh to the user and also are relatively expensive.
JBP 22-i 12Z6Z~L3 The balance of the compositions consist of water and may also contain minor amounts of owner components normally found in such compositions such as chelating agents, thickening agents, fragrances, coloring agents and the like.
The pi of the compositions should be maintained with-in a range of from about 4 to 8, preferably 7.0 to 7.5.
The present invention is more particularly described and explained by means of the following examples:
EXAMPLE I
An antimicrobial composition is prepared as follows:
a Methuselah (hydroxypropyl methyl cellulose) solution containing 1.9 g., active sufficient to provide 0.75%
wow Methuselah in the finished product is added to 75 g. deionized water and mixed until homogeneous. To this solution is added 50 g. active of a 20% active polyhexamethylene biguanide hydrochloride sold under the trade name Cosmocil CQ by ICY Americas Inc., Wit-mington, Delaware, followed by the addition of 0.25g. Versene 100 and 16.75 g. of 30% active cocoamido-propyldimethyl amine oxide. The pi is adjusted to 6.0 using 15% Hal and the total is adjusted to 250 g.
by the addition of deionized water. The resulting composition is of the following formula:
% w/w Cosmocil CQ 4.00 Versene 100 0.03 hydroxypropyl methyl cellulose 0.75 cocoamidopropyldimethyl 2.00 amine oxide deionized water us to 100 --- r ~226Z~3 EXAMPLE II
An antimicrobial composition is prepared according to the procedure of Example I except the cocoamidopropyldimethyl amine oxide is eliminated and replaced with deionized water.
EXAMPLE III
An antimicrobial composition is prepared according to the procedure of Example I except the Cosmocil CQ is elm-noted and replaced with deionized water EXAMPLE IV
An antimicrobial composition is prepared according to thepr~cedure of Example I except that 33.25 g. of cocoamido-propyldimethyl amine oxide are utilized resulting in a 1:1 ratio of amine oxide to Cosmocil CQ (on an "active"
basis).
EXAMPLE V
An antimicrobial composition is prepared according to the procedure of Example I except that 66.6 g. of amine oxide are utilized resulting in a 2:1 ratio of amine oxide to Cosmocil CQ (on an "active" basis).
EXAMPLE VI
A screening technique is used to test the compositions in Examples I-V. This technique consists of preparing 2-fold or 4-fold serial dilutions of the compositions of each Example. Allocates of these dilutions are then inoculated with a mixed suspension of gram positive bacteria or a mixed suspension of gram negative bacteria. The inoculm JBP I
1~26Z~3 density is adjusted to yield approximately 107 bacteria/ml of sample. Portions of the inoculated sample are then tested for viable bacteria at zero-time (immediately after inoculation), 6 to 8 minutes, 15 minutes, 30 minutes and 60 minutes after inoculation. This testing involves placing a calibrated 0.01 ml transfer loop into the inoculated sample and removing a remeasured portion which is then streaked on a solid growth medium (ajar) and incubated for a period of 48 hours at a temperature of 35~C. After the incubated period, the plates are examined for the presence or absence of growth. Any amount of growth on the line of streak is considered as positive growth. When the compositions of Examples I-V are tested according to the above procedure the following results are lo obtained. These results are expressed in terms of the minimum inhibitory concentration required for complete kill expressed in micrograms per milliliter (mcg/ml).
TABLE I
Composition Gram Positive Gram Negative time minutes time minutes Example I >104 104 156 39 <19 2500 312 39 <19 <19 Example II >104 5000 625 78 156 2500 39 <19 <19 <19 Example III >104 >104 5000 1250 1250 >104 >104 >104 >104 >104 Example IV >104 625 19 <19 <19625 <19 <19 ~19 <19 Example V >10 4 1250 19 <19 it 5000 <19 <19 <19 <19 ~ZZ~Z~3 These results clearly demonstrate the antimicrobial ad van-taxes of the compositions of the present invention, i.e., the compositions of Examples I, IV and V.
EXAMPLE VII
An antimicrobial composition is prepared according to the procedure of Example I and is of the following formulation:
wt/wt Chlorhexidine gluconate 4.00 Versene 100 0.03 15 hydroxypropylmethyl cellulose 0.75 cocoamidopropyldimethyl 4.00 deionized water us to 100 The pi of the above formulation is adjusted to l6.0 with dilute Hal.
EXAMPLE VIII
An antimicrobial composition is prepared according to the procedure of Example VII except that the cocoamidopropyl-dim ethyl amine oxide is utilized in a 1:2 ratio of amine oxide to chlorhexidine gluconate (on an "actves" basis).
EXAMPLE IX
An antimicrobial composition is prepared according to the procedure of Example VII except the cocoamidopropyldi-methyl amine oxide is eliminated and replaced with deionized water.
12;~6Z:~3 EXAMPLE X
An antimicrobial composition is prepared according to the procedure of Example VII except the chlorhexidine gluconate is eliminated and replaced with deionized water.
EXAMPLE XI
The compositions of Examples VII, VIII, IX and X are tested according to the procedure of Example VI and give the following results.
BP 2_.' - ~Z26Z~3 o o ox ox o o _ o o SHEA o Us r7 o us Al U') cry o Z O
En a N
I O
" I_ O
to Lo A
O Us O O O
O O O
ED Irk In Us I N
o a o H I O
O I O O
Eye I o o I_ Us Al a Jo I o o O O
En E QJ co a m o o 5 6 I o o I
PA
o o o o o o o o o A
C: H H
I) H X
I
Us O Q
I
O X X X X
.
lZ2~Z~3 Various other features and embodiments of the present invention not specifically set forth will be obvious to those skilled in the art, all of which may be achieved without departing from the spirit and scope of the invention as defined by the following claims.
JBP 22i
Claims (6)
1. An antimicrobial composition, comprising as active ingredients (a) a bis-biguanide compound selected from the group consisting of polyhexamethylene bigua-nidehydrochlorides of the formula:
wherein n is from 4.5 to 6.5, and chlorhexidine salts selected from the group consisting of chlorhexidine acetate, chlorhexidine hydrochloride and chlorhexidine gluconate and (b) an amine oxide of the formula:
wherein R is from 7 to 17 carbon atoms or mixtures thereof, the amine oxide and the bis-biguanide being present in a ratio of from about 1:2 to 4:1.
wherein n is from 4.5 to 6.5, and chlorhexidine salts selected from the group consisting of chlorhexidine acetate, chlorhexidine hydrochloride and chlorhexidine gluconate and (b) an amine oxide of the formula:
wherein R is from 7 to 17 carbon atoms or mixtures thereof, the amine oxide and the bis-biguanide being present in a ratio of from about 1:2 to 4:1.
2. The composition of claim 1 wherein the amine oxide is present in an amount of from about 1 to 20% by weight of the total composition.
3. The composition of claim 1 wherein the bis-biguanide is present in an amount of from about 2 to 5% by weight of the total composition.
4. The composition of claim 1 wherein the bis-biguanide is chlorhexidine gluconate.
5. The composition of claim 1 wherein the bis-biguanide is chlorhexidine hydrochloride.
6. The composition of claim 1 wherein the amine oxide is cocoamidopropyldimethyl amine oxide.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42337982A | 1982-09-24 | 1982-09-24 | |
| US423,379 | 1982-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1226213A true CA1226213A (en) | 1987-09-01 |
Family
ID=23678691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000437379A Expired CA1226213A (en) | 1982-09-24 | 1983-09-22 | Antimicrobial compositions |
Country Status (2)
| Country | Link |
|---|---|
| CA (1) | CA1226213A (en) |
| DE (1) | DE3334555A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5885562A (en) * | 1995-04-03 | 1999-03-23 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Deodorant compositions |
| EP3231452A1 (en) | 2016-04-11 | 2017-10-18 | DiCosmo, Frank | Wound irrigation solutions |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1259542A (en) * | 1984-09-28 | 1989-09-19 | Francis X. Smith | Disinfecting and preserving solutions for contact lenses and methods of use |
| SE8503256L (en) * | 1985-07-01 | 1987-01-02 | Dermaci Ab Ideon | MIXTURE OF CHLOREXIDE AND TRIS BUFFER FOR USE IN THE VAGINA, SKIN AND OTHER MUSCLES WITH ADDED PH |
| FR2633308B1 (en) * | 1988-06-28 | 1990-11-09 | Henkel France | PROCESS FOR THE TREATMENT OF MAMMALIAN UDDS, ESPECIALLY COW UDDS AND A COMPOSITION FOR CARRYING OUT THIS PROCESS |
| DE19902904A1 (en) * | 1999-01-26 | 2000-08-03 | Henkel Kgaa | Bleach and disinfectant |
| FR2978050B1 (en) * | 2011-07-19 | 2013-11-08 | Anios Lab Sarl | CLEANING AND / OR DISINFECTING COMPOSITION |
-
1983
- 1983-09-22 CA CA000437379A patent/CA1226213A/en not_active Expired
- 1983-09-23 DE DE19833334555 patent/DE3334555A1/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5885562A (en) * | 1995-04-03 | 1999-03-23 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Deodorant compositions |
| EP3231452A1 (en) | 2016-04-11 | 2017-10-18 | DiCosmo, Frank | Wound irrigation solutions |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3334555A1 (en) | 1984-05-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |